1. Field of the Invention
This invention relates to a process for preparing an organic compound as a product by reacting a starting organic compound in the presence of a phosphine oxide represented by formula (1). In particular, this invention relates to an effective process for preparing an oxyalkylene derivative by reacting an epoxy compound with an alcohol, thiol, phenol, thiophenol, carboxylic acid, sulfonic acid, carboxylate, carboxylic anhydride, sulfonate or carbonate. The oxyalkylene derivative is significantly important as, for example, an intermediate for preparation of a herbicide or medicament and a starting material for a polymer.
2. Description of the Prior Art
A phosphine oxide represented by formula (1) has been described only in G. N. Koidan et al., Journal of General Chemistry of the U.S.S.R., vol.55, p.1453 (1985). It describes that tris[tris(N,N-dimethylamido)phosphazo]methoxy-phosphonium iodide may be prepared by reacting methyl iodide with a phosphine oxide represented by formula (1), specifically tris(hexamethyltriamido-phosphazo)phosphate (also named as tris[tris(dimethylamino)phosphoranylideneamino]phosphine oxide where X.dbd.O). It, however, does not describe reacting analogous organic compounds except the phosphine oxide in the presence of the phosphine oxide represented by formula (1) or reacting an organic compound except the phosphine oxide with another organic compound except the phosphine oxide. Of course, it or any other document does not describe use of the phosphine oxide represented by formula (1) as a catalyst or polymerization initiator in an organic reaction.
It is known that for example an acid such as boron trifluoride or a base such as tertiary amines and tertiary phosphines may enhance a reaction of an epoxy compound with an alcohol, thiol, phenol, thiophenol, carboxylic acid or sulfonic acid to prepare an oxyalkylene derivative. The conventional acid or base catalysts, however, exhibit inadequate activity.
It is also known that for example tertiary amines, quaternary ammonium salts and quaternary phosphonium salts may enhance a reaction of an epoxy compound with a carboxylate, carboxylic anhydride, sulfonate or carbonate to prepare an oxyalkylene derivative (see K. Funabashi, Bulletin Chemical Society of Japan, vol.52, p.1488 (1979); T. Nishikubo, Yuki Gosei Kyokai Shi, vol.49 (3), p.219 (1991)). However, such a catalyst as the tertiary amines, quaternary ammonium salts and quaternary phosphonium salts also exhibits inadequate activity.
It is, therefore, necessary in either case to increase the amount or concentration of the catalyst or to conduct the reaction under severe conditions, which causes undesirable side reactions and/or degradation of reactants or products.